


Never Have I Ever

by BettyMonroe



Category: Supernatural
Genre: Anal Sex, Angst with a Happy Ending, Drinking Games, Ejaculate, F/M, Fluff and Angst, Love Confessions, Love at First Sight, Masturbation, Premarital Sex
Language: English
Status: Completed
Published: 2017-05-30
Updated: 2017-05-30
Packaged: 2018-11-07 00:40:45
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,090
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11047704
Author URL: https://archiveofourown.org/users/BettyMonroe/pseuds/BettyMonroe
Summary: Dean and Reader take a break from a long trip.  Things turn sexy when the reader suggests a drunken game of "Never Have I Ever".





	Never Have I Ever

I was beat. Dean and I had been driving all over Iowa for what seemed like forever on a never-ending battle of monsters. First it was the Shapeshifter in Des Moines, the vengeful spirit in Altoona, and a witch in Ankeny. Everything seemed to be heading north and I had not had more than 8 hours of sleep in 6 days. Finally, there was a break in all the calls and I was ready for some downtime. Sam was tying up some loose ends in Boone so we planned on meeting him there and finding a place to stay for a night or two.  
“God, I need a beer!” Dean said as we pulled into a liquor store parking lot. Boone was small and this store was the typical small town liquor store with the neighborhood hoodlums congregating outside the building.  
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“Please none of that craft crap you like! If that’s what you’re getting, grab me some bud light.” I teased. I had a crush on Dean since the first time we met. I needed help with a raw head in North Carolina, so I called John. His voicemail asked that anyone with an emergency to call Dean. I was almost knocked on my ass when we met up and I saw how fucking hot he was.  
I stayed in the car and went through his cassettes as he scrambled for some booze in the store. I felt slightly uneasy as I could feel the heavy stares of the kids who were loitering in front of the store. I looked in their direction slowly as not to let them realize I was looking at them. I had a feeling they were looking at Baby, and not directly at me. I was right. The smallest one who was about 5’ 5” and maybe weighed a buck twenty soaking wet came up to the car, wide eyed and in awe.  
“Sweet! That is a sexy ass ride!” He belted out.  
“Hey! Hey! Hey!” I could hear Dean shout as he walked out of the store, arms full of beer boxes. The kids stepped away and sneered at Dean.  
“Old geezer.” One of the kids said under their breath just loud enough for Dean and me to hear. Dean’s face was priceless. Surprised and pissed at the same time. He mumbled something under his breath as he opened the back door to put the beer on the floorboard. Dean got in the driver’s seat and paused before looking at me.  
“Remind me again why I don’t have kids. Oh, yeah! That’s why!” He was irritated. I slipped Zeppelin in the cassette player as we backed out down the main road. I knew Traveling Riverside Blues would cheer him up. “Squeeze my lemon as juice runs down my leg” oozed out of Baby’s radio as we pulled up to the divey motel. I saw him smirk out of the corner of my eye. I think he liked this song because the lyrics were overtly dirty.  
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Dean shut down the car and let out a sigh of relief. “You grab the booze, I’ll grab the bags?” he asked while putting the keys in his coat pocket.  
“Yeah, sounds good but I get dibs on the shower, you get dibs on the magic fingers.” I smiled and tossed him a roll of quarters I had hiding in the inside pocket of my jean jacket. His eyes lit up like Christmas morning. I always found it amusing, the things that made him happy: Magic fingers, steam showers, pie. Little things made him happy which I assumed was a bi-product of not having much of anything growing up.  
Our room was small but there were too beds that looked comfortable. The décor was very retro with pink floral wallpaper and blue shag carpet that I was sure had not been replaced since 1976.  
I chuckled a little, “Hey, I bet that carpet is older than you.” I smiled and looked at Dean.  
“Heh, heh, heh” he mocked as he put on a phony smile. “Pretty funny kid.” I smiled and set the beer on the small faux wood table in the corner of the room. Thank God, we had a small fridge in the room. I hated warm beer. I grabbed my bag and ran to the bathroom while Dean, smiling, plugged quarter after quarter into the little silver box on the headboard of his bed.  
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I tried to be fast but wanted to shave my legs so I could wear my shorts to bed. That was one thing I missed about working alone. No one to see my hairy legs but me. I towel dried my hair and slipped into my pink camisole and jogging shorts. My wet ringlets dripped little droplets of water on my shirt. It had been about 20 minutes and as I opened the door, Dean was still laying on the bed, eyes closed, singing Asia under his breath. He continued as I walked to the fridge to pull out a couple of beers.  
“Ahem!” I cleared my throat as I sat down at the table, gesturing to Dean with his bottle of foo foo beer. He jumped up as if he had been bitten and looked a little embarrassed.  
“Thanks, [YN]” he said quietly as he walked over to the table, stretching his arms over his head. “This week has just beaten the shit out of me.”  
“I know, right?” I said as I tipped the long-necked bottle to my lips and propped my bare feet onto the table.  
“I need some fun.” Dean scooted back in his chair to the clock radio on the nightstand beside my bed. He fiddled with the dial until he found what we assumed was the oldies station since they were playing Dokken. Another smile crossed his perfect lips as he scooted back to the table.  
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“Ever played ‘Never Have I Ever’?” I asked, taking another big gulp of beer. I smiled at Dean while again he looked puzzled. “Since we are drinking, it might be fun. One of us starts by saying, ‘Never have I ever’ then say something you have never done that you think the other person may have done. If that person has ‘done’ it, they drink. If not, you drink”.  
“Sounds fun,” Dean chuckled as he looked at my feet on the table, “you start.”  
“Oh, let’s see… Never have I ever killed a vampire”. I knew I had him on this one. Being new to the business, I didn’t have the pleasure of killing as many baddies as Sam and Dean. I was a little jealous.  
“Funny” Dean said as he took swig of his beer. “My turn? Never have I ever… slept with a monster.”  
“In my defense, it was only one time and I didn’t know he was a monster until after I slept with him.” I smiled and realized my bottle was empty. Looking at Dean’s bottle, he needed a refill too. I shook my bottle at him and grabbed two more bottles of each beer, closing the fridge door with my foot. Sitting down, I placed all the beers on the table, grabbed one and drank. Before I could swallow, I realized I took a huge gulp of Dean’s nasty craft beer. He smiled wide.  
“That would be mine”. He grabbed the bottle from my hand and pushed a Bud Light over to me.  
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About 20 minutes went by. Silly question after silly question. Things that we knew each other would have to drink to. As my sobriety waned, the questions got racier. Never have I ever had sex in a car, … had sex with someone I saved, been turned on by killing a monster.  
“Never have I ever been in love.” Shit! Did I just say that?! I knew Dean’s history with Lisa and it broke my heart that I actually asked this. “Sorry”, I said to Dean as he turned his head to look outside and finished the bottle of beer I had started. “You can ask me a crazy one.”  
He sat for a moment, eyes sullen. I knew he was hurt, but then Dean Smiled, “Never have I ever tried anal”.  
My face was hot and my cheeks flushed bright crimson, “Giving or receiving?” I asked jokingly, knowing Dean would get into a tizzy.  
“Neither!” His eyes widened as he looked at me in disbelief. I believed it was due to being surprised he had to clarify both for himself and for me.  
“Me neither but I have been curious.” The words dripped off my lips and Dean’s eyes, though I didn’t think it were possible, got even bigger.  
Dean took another bottle and drank about half in one swig. His lips parted and I thought I was going to explode.  
“Me too.” Dean looked at me with a look I had only ever seen him have when washing Baby. He reached out and traced the curve on the bottom of my bare foot.  
I put my feet down on the floor slowly and sat up to lean in staring into his eyes. “Never have I ever had sex with my hunting partner.” Dean didn’t flinch. He stared back into my eyes as he reached under the table putting a hand on my leg. A seemingly eternal silence followed.  
“Let me know if I’m crossing the line here, but I want nothing more than to fuck you on this table right now.” The words rolled off his tongue and my belly flopped. I jumped up when I realized he was dead serious and grabbed his face, kissing him deep as I pulled him out of his chair. We stumbled as he fell backward onto my bed and he wrapped his arms around my waist so we would fall together.  
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I could taste the after-bite of his bitter beer as his tongue met mine, pushing and fighting each other until he won and sucked my entire tongue into his mouth. His delicious lips pressed mine and I moaned. Dean pulled back, letting go of his anaconda grip on my tongue. Flipping me over with one arm so that I was on the bed, he pushed me back so only my feet hung off the foot of the bed. He kissed the bottom of each foot gently before kissing the tips of my toes. Sucking gently on my second toe, he reached up my thigh under the leg of my shorts. I sat up and grabbed the sides of his open purple flannel and pulled his body on top of me; his weight pressing me into the bed. Suddenly I could feel his hardness through his jeans, pressing into my pelvic bone. I grabbed his ass and pushed his weight further into me as he ground his cock up against me. I felt my nipples harden and realized and panties were soaked.  
Dean sat up and took off his flannel revealing an AC/DC t-shirt underneath. He feverishly unbuckled his belt and tossed it next to me before undoing his jeans. Pulling them off, I could see the outline of him under his boxers. I was ready for this and a second wave of intoxication hit me. I pulled off my cami and my curls dropped over my bare breasts. His green eyes focused on my breasts and a look of determination struck his face. He wanted me too. In one fast motion, he grabbed the waist of my shorts and pulled off both my shorts and my panties at once, leaving me totally naked on my bed. He paused while I looked up at him with purpose and gave a little nod.  
He slowly lowered himself to kiss my navel as he worked his way up to my nipples. I could feel his hand once again slide up my thigh, resting an inch shy of my bikini line. Looking up at me, he continued until he slipped two fingers inside of me, while sliding his thumb onto my clit. I let out a seemingly disembodied moan. Dean closed his eyes savoring the moment while his fingers glided in and out of me. My core clenched and I could feel myself release, squeezing his fingers as he continued to work his magic. Once I was finished and began catching my bearings, he slowly pulled out his fingers offering them to me. I took each slippery finger into my mouth one by one, enjoying taste of myself for the first time. The salty sweetness was not what I had expected, but it turned me on even more.  
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Dean stood up to pull off his boxers and I stared as he slowly unveiled the full size of his dick. I got up on all fours facing him, licking my lips as I stared hungrily at the masterpiece. He reached out to place his hand on my shoulder, while grabbing himself with the other hand.  
“Oh, no honey. Not yet.” He slid his hand up then down the length of his shaft and the veins bulged. “I want to be each other’s first”. He slowly sat next to me on the bed and reached for my hand to pull me on top of him. I spun around to sit on his lap with my back facing him, but he quickly pulled me around so we were chest to chest. “No baby, I want to see your beautiful face” he said as he smiled sweetly, looking into my eyes.  
I grabbed his bare shoulders and lowered myself onto his shaft. Dean’s eyes rolled back and he let out a small groan as I slide myself all the way to his balls. I could feel him fill me to the point that I didn’t think he could go any deeper. I began riding him, his eyes never leaving mine. He grabbed the back of my head to pull my face near his then buried his face in my neck, his lips devouring my collarbone. I felt another build up and just as I was about to come, he lifted me off his lap and pulled my body closer.  
“You ok?” he panted. I nodded my head and he slowly pulled me back down on top of him, this time, the tip of his head slowly entering my ass. He grabbed both sides of my ass, stretching me to fit his thickness. I relaxed as I felt him push deeper and deeper until his head was all the way in. I was thankful for how wet I was, or else it may have been less pleasurable. My skin seared slightly as he continued to lower me on top of him until he was fully in me. I screamed and he stopped with a worried look.  
“No, don’t stop!” I screamed. Flickers of pain and unimaginable sensations filled my body repeatedly as he thrust in and out of my ass. I could feel my come running like a river out of me and onto his pelvis as I screamed “Dean, yes, oh my GOD!”. He leaned back to lay himself fully on the bed to let me take control of his body as I lost control of mine. He gritted his teeth as I began to writhe on him. I reached down to feel how wet I was and without realizing it, my own fingers were buried deep inside me, feeling the fullness of Dean on the other side. He began thrusting back as he was ready to explode, then sat up swiftly, matching his thrusting to my strokes.  
“[YN]!!!!!!” He yelled as I could feel him let go. He pushed down one last thrust as he wrapped his arms tighter around me until I thought I would pass out. We both sat a moment breathing heavily. Finding ourselves and realizing what had just happened, we smiled at each other, out of breath and dripping with sweat. He loosened his grip on me as he leaned in to kiss me gently on the lips then the forehead, then pulled me closer again for another embrace. I stood up slowly and walked awkwardly to the bathroom to clean up. I brought him a wash cloth and we faced away from each to gather our composure and get dressed. I found my shorts on the foot of my bed and stepped into them. As I pulled them up, I turned to see Dean pulling up his boxers. He walked over to me slowly.  
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“I’ve wanted to do that for a long time”.  
I stepped back a little. “oh, so you have been curious for a while, huh?” I joked.  
He smiled, “Well, yeah, no. Not that. You, I’ve wanted you for as long as I could remember. You asked me earlier about being in love,” he stepped closer to me and reached out to hold my waist, “I don’t want to scare you but the way I feel when I’m with you, kicking monster hide together… There is a place inside me that only feels fulfilled… when I’m with you.” I stood there, not knowing what to say. Here was this gorgeous man confessing his love to me.  
“Me too” I answered quietly. Dean smiled just as big as he did when I handed him the quarters earlier. He pulled me close in his arms and we stood there embracing for what I wanted to be an eternity.  
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It was late and we both needed to rest. Sam would be home soon. Was Dean going to say anything? Would Sam think something was going on? I wasn’t sure but I couldn’t remember when I felt happier. We both laid down on my bed, his arm stretched under my neck while he stared at the ceiling. Me on my side with my hand resting on his chest.  
“So, I think both of us won that round,” I said smiling to myself and poking Dean gently on the chest.  
I looked up and Dean smiled. “Yeah, I never thought I would get to break down your back door.” I punched him in the shoulder and he laughed harder than I had ever heard him laugh before. “Ow!” he chuckled as he shook out his arm. “So, where do we go from here?”  
I looked back up at the ceiling, not knowing how to answer. I only knew that I wanted this with my entire being. After all, a hunter’s life is mainly not knowing what’s next.


End file.
